What’s the worst that could happen? That’s what we ask our friends when they consider some adventurous jump into the unknown.

Friend: I’ve got this job opportunity. But it’s only two years and it’s in South America. Should I take it?

You: Sure! What’s the worst that could happen?

The question feels so easy when we say it to other people. So obvious. But what about when our friends say it to us? What’s the worst that could happen? No really. Think about it.

One Small Step for Some. One Giant Leap for Me

I’ve been thinking about it since July 30th because that’s when I started this site. It doesn’t look like much but it took me four years to get to this point. I learn something every day that I want to share but I seldom did. Not after the mistake I made some time ago.

You see, I used to do this. I wrote a number of things online for established professional sites. It was fun. They were great.

Until I made a mistake that put me in a bit of a bind. It was just this one time, this one moment where I published a postmortem of a failed project. The article strayed close to The Line. Rather than being broad insights based on new information, it was really specific and really open.

It created some pressure. I unintentionally let some people down. So I retreated. I went offline and stuck to print publishing. But people took notice and, over the years, many have asked me to come back. They said I should start sharing again. It was incredibly gratifying to hear.

So over the past two weeks, I shared this site with friends who said “This is nice, Norm, but you should put your name on it. None of this pseudonym stuff. Get yourself out there.”

And while no one used the line, I heard it loud and clear: What’s the worst that could happen?

I wrote some answers. I then thought about how I would respond in each case, how I would protect against it, or catch the warning signs beforehand. Suddenly, I was empowered. Suddenly, the fear was known. I met it. And it was, as always, totally overrated.

What’s the worst that could happen? Considering the downside, the worst, is an powerful practice that predates modernity. It goes by the name premeditatio malorum. Negative visualization. It’s a cornerstone of the Stoic philosophy and what helped one of the greatest emperors of Rome, Marcus Aurelius.

His journal to himself, Meditations, is the embodiment of premeditatio malorum. But it isn’t just negative visualization that counts. Positive visualization matters, too. Here’s a favorite quote from the emperor: Look back over the past with its changing empires that rose and fell and you can foresee the future.

I look back on previous efforts, mine and others, and foresee a future where I will absolutely fail in providing this service if I repeat certain mistakes. I also see a future where I will thrive if I repeat certain successes. This foresight allows me to strive strategically1hence the title of this site towards the goal to write the most useful thing you read on a given day.

How Will It Fail?

Try to say it: premeditatio malorum. Sounds nice, right? Again, that’s the latin term for this technique. A more modern term comes from psychologist Gary Klein. He calls it the premortem from his fabulous book Source of Power. 2this will be my next book review

When considering a decision, the premortem is a technique that poses the question: “How will this fail?” In my case, how will this blog lead to disaster?

That’s easy. This blog will fail if it exists a blog. This isn’t supposed to be a blog. Blogs are for healthy indulgences, personal thoughts, feelings, and the sort of catharsis that manifests itself in articles that are more rants than ideas.

So this won’t be a blog. It will be a service to friends, colleagues, and anyone curious.

How Will It Succeed?

If I can do that in a way that makes this the most useful thing you read today, then it will be a success. Why? Because history shows that’s what success looks like. That’s the work that is printed in the magazines. That’s the work that people thank me for. Total strangers find me occasionally and say what a nice thing I did. It blows me away. That’s the success.

Besides, what’s the worst that could happen? When I define that absolute fear (I’ll be laughed at, scorned, ignored, contradicted, challenged, given the ol’ hairy eyeball at my next meeting), I know the unknowns.

Then the fear isn’t so great. Then I can take the jump. And I can invite you to take it with me. I’ll have another post tomorrow. The next day, too. I’ll make one every day I can.

Special thanks to everyone who helped me get here. Your help means a lot.